Patent DE-19925329-A1 (DE)
Title: New triazine derivatives useful as selective herbicides and plant growth regulators
Inventor: GIENCKE WOLFGANG
IPC: C07D407/12
Filed: 1999-06-02
Abstract: 2-Amino-1,3,5-triazine derivatives (I) are new. 2-Amino-1,3,5-triazine derivatives of formula (I) and their salts are new: R1  = optionally substituted aryl, 3-9C cycloalkyl or heterocyclyl; or 1-6C alkyl, 2-6C alkenyl or 2-6C alkynyl optionally substituted by halogen, OH, CN, NO2, SCN, 1-4C alkoxy, 1-4C haloalkoxy, 2-4C alkenyloxy, 2-4C haloalkenyloxy, 1-4C alkylthio, 1-4C alkylsulfinyl, 1-4C alkylsulfonyl, 1-4C haloalkylsulfinyl, 1-4C haloalkylsulfonyl, optionally substituted 3-9C cycloalkyl, optionally substituted phenyl, optionally substituted heterocyclyl, C(Z')R', ZC(Z')R', C(Z')ZR', C(Z')NR'R, OC(Z')ZR', ZC(Z')NR'R, N(R)C(Z')ZR' and/or N(R')C(Z')NR'R;  R', R, R'  = optionally substituted 1-6C alkyl, aryl, aryl(1-6C)alkyl, 3-9C cycloalkyl or (3-9C)cycloalkyl(1-6C)alkyl;  Z, Z'  = O or S;  R2  = optionally substituted 3-9C cycloalkyl, 4-9C cycloalkenyl, heterocyclyl or phenyl;  R3  = H; optionally substituted 1-6C alkyl, aryl or 3-9C cycloalkyl; or N(B1D1)(B2D2) or N(R)N(B1D1)(B2D2);  R  = H, 1-6C alkyl or 2-5C alkanoyl;  R4  = B3D3;  A1  = linear 1-5C alkylene, 2-5C alkenylene or 2-5C alkynylene optionally substituted by halogen, NO2, CN, SCN and/or B4D4;  A2  = a bond; linear 1-4C alkylene, 2-5C alkenylene or 2-5C alkynylene optionally substituted by halogen, NO2, CN, SCN and/or B5D5; or CR6R7-W asterisk -CR8R9, CR10R11-W asterisk -CR12R13-CR14R15, CR16R17-CR18R19-W asterisk -CR20R21, CR22R23-CR24R25-W asterisk or CR26R27-W asterisk ;  R6-R27  = H, halogen, NO2, CN, SCN or B6D6 W asterisk  = O, S or N(B7D7);  B1, B2, B3, B7  = bonds, C(Z asterisk ), C(Z asterisk )Z asterisk asterisk , C(Z asterisk )NH or C(Z asterisk )NR asterisk ;  Z asterisk , Z asterisk asterisk  = O or S;  R asterisk  = optionally substituted 1-6C alkyl, aryl, aryl(1-6C)alkyl, 3-9C cycloalkyl or (3-9C)cycloalkyl(1-6C)alkyl;  B4, B5, B6  = bonds, O, SOp, SOpO, OSOp, CO, OCO, COO, SCO, COS, SCS, CSS, OCOO, NR0, ONR0, NR0O, NR0CO, CONR0, OCONR0 or NR0COO;  p  = 0-2;  R0  = H or optionally substituted 1-6C alkyl, aryl, aryl(1-6C)alkyl, 3-9C cycloalkyl or (3-9C)cycloalkyl(1-6C)alkyl;  D1-D4, D6  = = H or optionally substituted 1-6C alkyl, aryl, aryl(1-6C)alkyl, 3-9C cycloalkyl or (3-9C)cycloalkyl(1-6C)alkyl;  D5  = H or optionally substituted 1-6C alkyl, aryl, aryl(1-6C)alkyl, 3-9C cycloalkyl or (3-9C)cycloalkyl(1-6C)alkyl, or D5+D5 = 2-4C alkylene optionally substituted by 1-4C alkyl and/or 1-4C alkoxy;  X  = halogen, OH, NH2, NO2, CHO, COOH, CN, SCN OR CONH2; optionally substituted 1-6C alkyl, 1-6C alkoxy, 1-6C alkylthio, mono- or di(1-6C alkyl)amino, 2-6C alkenyl, 2-6C alkynyl, 2-7C alkanoyl, 2-7C alkoxycarbonyl, mono- or di(1-6C alkyl)carbamoyl, 1-6C alkanoylamino or N-(1-6C alkanoyl)-N-(1-4C alkyl)amino; or optionally substituted 3-9C cycloalkyl, 3-9C cycloalkoxy, 3-9C cycloalkylamino, phenyl, phenoxy, phenylthio, benzoyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino; or adjacent X+X forms a 4- to 6-membered fused ring that optionally contains O, S and/or N atoms and is optionally substituted by halogen, 1-4C alkyl or oxo; n = 0-5;  heterocyclyl  = a 3- to 7-membered ring containing 1-3 heteroatoms selected from N, O and S;  A1 and A2R2 contain a total of at least 6 C atoms or A1 and A2R2 contain a total of 5 C atoms and A1  = CH2 or CH2CH2 and R1 = optionally substituted 1-4C alkyl, 1-4C haloalkyl, 2-6C haloalkenyl or 3-9C cycloalkyl. Independent claims are also included for the following: (1) a process for preparing compounds (I); (2) intermediates of formula (III) and (V):